Enantioselective synthesis of chiral α,β-unsaturated γ-substituted butyrolactams by organocatalyzed direct asymmetric vinylogous Michael addition of α,β-unsaturated γ-butyrolactam to 2-enoylpyridines

2016 ◽  
Vol 14 (27) ◽  
pp. 6568-6576 ◽  
Author(s):  
Zhen-Hua Wang ◽  
Zhi-Jun Wu ◽  
Deng-Feng Yue ◽  
Yong You ◽  
Xiao-Ying Xu ◽  
...  
Keyword(s):  
Michael Addition ◽  
Optically Active ◽  
Enantioselective Synthesis ◽  
High Yields

Approach providing a series of optically active α,β-unsaturated γ-substituted butyrolactams in high yields with excellent diastereo- and enantioselectivities.

scholarly journals Enantioselective synthesis of seven-membered carbo- and heterocyles by organocatalyzed intramolecular Michael addition

RSC Advances ◽  
2016 ◽  
Vol 6 (36) ◽  
pp. 30166-30169 ◽  
Author(s):  
James O. Guevara-Pulido ◽  
José M. Andrés ◽  
Deisy P. Ávila ◽  
Rafael Pedrosa
Keyword(s):  
Michael Addition ◽  
Enantioselective Synthesis ◽  
High Yields

Enantioenriched seven membered rings have been prepared in high yields and stereoselectivities by intramolecular Michael addition of functionalized enals catalyzed by Jorgensen–Hayashi catalyst.

Expeditious assembly of fused dihydropyranones via N-heterocyclic carbene-catalyzed tandem Michael addition/lactonization

2017 ◽  
Vol 15 (6) ◽  
pp. 1329-1333 ◽  
Author(s):  
Qiao Ren ◽  
Muyao Li ◽  
Lujiang Yuan
Keyword(s):  
Michael Addition ◽  
Optically Active ◽  
High Yields

A convergent and efficient NHC-catalyzed enantioselective tandem Michael addition/lactonization sequence of ynals with 1,2-dione is disclosed. This strategy expeditiously assembles the valuable optically active fused dihydropyranones in good to high yields and with excellent enantioselectivities.

Asymmetric Brønsted Acid-catalyzed Intramolecular aza-Michael Reaction – Enantioselective Synthesis of Dihydroquinolinones

2012 ◽  
Vol 67 (10) ◽  
pp. 1021-1029 ◽  
Author(s):  
Magnus Rueping ◽  
Stefan A. Moreth ◽  
Michael Bolte
Keyword(s):  
Michael Addition ◽  
Heterocyclic Compounds ◽  
Michael Reaction ◽  
Biological Activities ◽  
Enantioselective Synthesis ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Acid Catalyzed ◽  
High Yields

The enantioselective synthesis of 2-aryl-substituted 2,3-dihydroquinolin-4-ones, a class of heterocyclic compounds with interesting biological activities, has been achieved through a Brønsted acidcatalyzed enantioselective intramolecular Michael addition. The products are available in moderate to high yields and with good enantioselectivities.

scholarly journals Organocatalytic atroposelective heterocycloaddition to access axially chiral 2-arylquinolines

2021 ◽  
Vol 4 (1) ◽  
Author(s):  
Gongming Yang ◽  
Shaofa Sun ◽  
Zhipeng Li ◽  
Yuhan Liu ◽  
Jian Wang
Keyword(s):  
Drug Discovery ◽  
Asymmetric Synthesis ◽  
Vital Role ◽  
Optically Active ◽  
Enantioselective Synthesis ◽  
Chiral Amine ◽  
New Class ◽  
Axially Chiral ◽  
High Yields

AbstractAxially chiral heterobiaryls play a vital role in asymmetric synthesis and drug discovery. However, there are few reports on the synthesis of atropisomeric heterobiaryls compared with axially chiral biaryls. Thus, the rapid enantioselective construction of optically active heterobiaryls and their analogues remains an attractive challenge. Here, we report a concise chiral amine-catalyzed atroposelective heterocycloaddition reaction of alkynes with ortho-aminoarylaldehydes, and obtain a new class of axially chiral 2-arylquinoline skeletons with high yields and excellent enantioselectivities. In addition, the axially chiral 2-arylquinoline framework with different substituents is expected to be widely used in enantioselective synthesis.

scholarly journals Organocatalysts for enantioselective synthesis of fine chemicals: definitions, trends and developments

2015 ◽  
Author(s):  
Chiara Palumbo
Keyword(s):  
Asymmetric Catalysis ◽  
Scientific Community ◽  
Organic Molecules ◽  
Optically Active ◽  
Enantioselective Synthesis ◽  
Fine Chemicals ◽  
Organic Transformations ◽  
Small Organic Molecules ◽  
Substrate Activation ◽  
High Yields

Organocatalysis, that is the use of small organic molecules to catalyse organic transformations, has been included among the most successful concepts in asymmetric catalysis and it has been used for the enantioselective construction of C-C, C-N, C-O, C-S, C-P, and C-halide bonds. Since the seminal works in early 2000, the scientific community has been paying an ever-growing attention to the use of organocatalysts for the synthesis, with high yields and remarkable stereoselectivities, of optically active fine chemicals of interest for the pharmaceutical industry. A brief overview is here presented about the two main classes of substrate activation by the catalyst: covalent organocatalysis and non-covalent organocatalysis, with a more stringent focus on some recent outcomes in the field of the latter and of hydrogen-bond-based catalysis. Finally, some successful examples of heterogenisation of organocatalysts are also discussed, in the view of a potential industrial exploitation.

Enantioselective synthesis of 3-substituted 1,2-oxazinanes via organocatalytic intramolecular aza-Michael addition

2014 ◽  
Vol 12 (43) ◽  
pp. 8607-8610 ◽  
Author(s):  
Shuanghua Cheng ◽  
Shouyun Yu
Keyword(s):  
Michael Addition ◽  
Enantioselective Synthesis ◽  
High Yields

A highly enantioselective intramolecular 6-exo-trig aza-Michael addition was developed to afford chiral 3-substituted 1,2-oxazinanes in high yields (up to 99% yield) and good enantioselectivities (up to 98/2 er).

scholarly journals Organocatalysts for enantioselective synthesis of fine chemicals: definitions, trends and developments

2015 ◽  
Keyword(s):  
Asymmetric Catalysis ◽  
Scientific Community ◽  
Organic Molecules ◽  
Optically Active ◽  
Enantioselective Synthesis ◽  
Fine Chemicals ◽  
Organic Transformations ◽  
Small Organic Molecules ◽  
Substrate Activation ◽  
High Yields

<p>Organocatalysis, that is the use of small organic molecules to catalyse organic transformations, has been included among the most successful concepts in asymmetric catalysis and it has been used for the enantioselective construction of C-C, C-N, C-O, C-S, C-P, and C-halide bonds. Since the seminal works in early 2000, the scientific community has been paying an ever-growing attention to the use of organocatalysts for the synthesis, with high yields and remarkable stereoselectivities, of optically active fine chemicals of interest for the pharmaceutical industry. A brief overview is here presented about the two main classes of substrate activation by the catalyst: covalent organocatalysis and non-covalent organocatalysis, with a more stringent focus on some recent outcomes in the field of the latter and of hydrogen-bond-based catalysis. Finally, some successful examples of heterogenisation of organocatalysts are also discussed, in the view of a potential industrial exploitation.</p>

Lithiated three-membered heterocycles as chiral nucleophiles in the enantioselective synthesis of 1-oxaspiro[2,3]hexanes

2021 ◽  
Author(s):  
Andrea Cocco ◽  
Maria Grazia Rubanu ◽  
Maria Laura Sechi ◽  
Angelo Frongia ◽  
Pietro Mastrorilli ◽  
...  
Keyword(s):  
Styrene Oxide ◽  
Enantioselective Synthesis ◽  
High Yields

Enantiomerically enriched oxaspiro- and azaspirohexanes were synthesized through a two-step addition of configurably stable Li-styrene oxide (or aziridine) to 3-substituted cyclobutanones and base-mediated Payne rearrangement sequence with high yields and selectivity.

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